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87-91-2 - (+)-Diethyl L-tartrate, 98% - L-Tartaric acid diethyl ester - A10641 - Alfa Aesar

A10641 (+)-Diethyl L-tartrate, 98%

Numéro CAS
87-91-2
Synonymes
L-Tartaric acid diethyl ester

Dimensions Prix ($) Quantité Disponibilité
100g 38,20
250g 84,30
500g 151,00
1000g 245,00
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(+)-Diethyl L-tartrate, 98%

MDL
MFCD00009143
EINECS
201-783-3

Propriétés chimiques

Formule
C8H14O6
Poids formulaire
206.19
Point de fusion
17°
Point d'ébullition
280°
Point d'éclair
93°(199°F)
Densité
1.205
Indice de réfraction
1.4460
Solubilité
Fully miscible in water.

Applications

(+)-Diethyl L-tartrate is used as a chiral auxiliary in the Sharpless enantioselective epoxidation of allylic alcohols, for Sharpless-type enantioselective oxidation of sulfides to sulfoxides and as a chiral auxiliary in the enantioselective construction of cyclopropanes from allylic alcohols by an asymmetric Simmons-Smith reaction. It is also used as a chiral reagent in a host of chemical reactions, such as the synthesis of isoquinoline alkaloids and arundic acid, which has been used in acute ischemic stroke therapy.

Notes

Keep container tightly sealed. Store in cool, dry conditions in well sealed containers. Incompatible with oxidizing agents.

Références bibliographiques

Peter Somfai. An enantioselective total synthesis of (+)-altholactone from diethyl L-tartrate. Tetrahedron. 1994, 50, (38), 11315-11320.

Woo-Wha Lee.; Sukbok Chang. A new and concise synthetic route to an enantiopure (+)-conduritol-E derivative from diethyl l-tartrate. Tetrahedron: Asymmetry. 1999, 10 (23), 4473-4475.

For use as a chiral auxiliary in the Sharpless enantioselective epoxidation of allylic alcohols, see tert-Butyl­ hydroperoxide, A13926. For Sharpless-type enantioselective oxidation of sulfides to sulfoxides, see: Org. Synth. Coll., 8, 464 (1993).

For use as a chiral auxiliary in the enantioselective construction of cyclopropanes from allylic alcohols by an asymmetric Simmons-Smith reaction, see: Chem. Lett., 61 (1992). For a review of the use of tartrate esters as chiral auxiliaries, e.g. in the Simmons-Smith reaction and in 1,3-dipolar cycloaddition reactions, see: Synlett, 1075 (2003).

Mentions de danger et de prudence du SGH

Mentions de danger (UE): H227

Combustible liquid.

Mentions de prudence: P210-P280-P370+P378a-P403+P235-P501a

Keep away from heat/sparks/open flames/hot surfaces. - No smoking. Wear protective gloves/protective clothing/eye protection/face protection. In case of fire: Use for extinction: CO2, powder or water spray. Store in a well-ventilated place. Keep cool. Dispose of contents/container in accordance with local/regional/national/international regulations.

Autres références

Merck
14,3855
Beilstein
1727145
Code tarifaire harmonisé
2918.13
TSCA
Yes

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Analytique et matériel de laboratoire